1-(3-Bromo­prop­oxy)-4-iodo­benzene

In the title compound, C₉H₁₀BrIO, the dihedral angle between the benzene ring and its attached -O-CH₂-CH₂- group is 3.81 (19)°.

Key indicators

• Single-crystal X-ray study
• T = 113 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.025
• wR factor = 0.056
• Data-to-parameter ratio = 22.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.97
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.03
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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S1. Comment

The title compound, (I), is an intermediate in the synthesis of the dual-function H₁ antagonist/5-LO inhibitor compounds (Lewis et al., 2004) which would provide a valuable alternative to the currently available therapies on asthma. A view of the molecular structure of (I) is shown in Fig. 1. A l l bonds lengths and angles are normal.

Related literature

For related literature, see: Lewis et al. (2004).

S2. Experimental

To a suspension of (3-bromo-propoxy)-benzene (1.0 g, 4.6 mmol) and mercury(II) oxide (1.0 g, 4.6 mmol) in dichloromethane (30 ml) was added iodine (1.2 g, 4.6 mmol) and the resulting mixture was stirred at room temperature. After 40 h the reaction mixture was filtered to remove the insoluble material, and the filtrate was washed with Na₂S₂O₃ (20 wt % solution) and brine. The organic phase was then dried over anhydrous Na₂SO₄, filtered, and concentrated in vacuo. The pure product was obtained by column chromatography on silica gel with petroleum ether-ethyl acetate (20:1 v/v) as eluent to give the product (1.03 g, 65%). Colourless blocks of (I) were grown by slow evaporation of petroleum ether at room temperature over a period of 5 days.

S3. Refinement

The H atoms were positioned geometrically (C—H = 0.93–0.97 Å) and refined as riding with U_iso = 1.2U_eq(C).

Computing details

Data collection: CrystalClear (Rigaku, 2003); cell refinement: CrystalClear (Rigaku, 2003); data reduction: CrystalClear (Rigaku, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL (Bruker, 1997).

Figures

Fig. 1. A view of the molecular structure of (I). Displacement ellipsoids are drawn at the 30% probability level and H atoms are shown as spheres of arbitrary radius.

1-(3-Bromopropoxy)-4-iodobenzene

Crystal data

C9H10BrIO	F(000) = 640
Mr = 340.98	Dx = 2.219 Mg m^−3
Monoclinic, P21/c	Melting point: 340 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 9.1604 (18) Å	Cell parameters from 3015 reflections
b = 10.222 (2) Å	θ = 1.9–27.9°
c = 10.903 (2) Å	µ = 7.00 mm^−1
β = 90.68 (3)°	T = 113 K
V = 1020.9 (4) Å^3	Block, colourless
Z = 4	0.10 × 0.08 × 0.06 mm

Data collection

Rigaku saturn diffractometer	2398 independent reflections
Radiation source: rotating anode	1934 reflections with I > 2σ(I)
Confocal monochromator	Rint = 0.040
ω scans	θmax = 27.9°, θmin = 2.2°
Absorption correction: multi-scan (CrystalClear; Rigaku, 2003)	h = −12→11
Tmin = 0.541, Tmax = 0.679	k = −8→13
7486 measured reflections	l = −14→14

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.025	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.056	H-atom parameters constrained
S = 0.99	w = 1/[σ^2(Fo^2) + (0.0242P)^2] where P = (Fo^2 + 2Fc^2)/3
2398 reflections	(Δ/σ)max = 0.002
109 parameters	Δρmax = 1.46 e Å^−3
0 restraints	Δρmin = −0.72 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
I1	0.40187 (2)	0.04322 (2)	0.787855 (18)	0.02246 (8)
Br1	1.17228 (3)	0.12604 (3)	0.04937 (3)	0.02077 (9)
O1	0.8837 (2)	0.1443 (2)	0.40015 (18)	0.0175 (4)
C1	0.6576 (3)	0.2147 (3)	0.4965 (3)	0.0180 (6)
H1	0.6523	0.2904	0.4493	0.022*
C2	0.5516 (3)	0.1885 (3)	0.5830 (3)	0.0182 (6)
H2	0.4749	0.2469	0.5937	0.022*
C3	0.5592 (3)	0.0770 (3)	0.6528 (3)	0.0169 (6)
C4	0.6714 (3)	−0.0122 (3)	0.6366 (3)	0.0181 (6)
H4	0.6750	−0.0883	0.6832	0.022*
C5	0.7780 (3)	0.0127 (3)	0.5506 (3)	0.0177 (6)
H5	0.8537	−0.0465	0.5393	0.021*
C6	0.7710 (3)	0.1273 (3)	0.4809 (3)	0.0141 (6)
C7	0.8748 (3)	0.2560 (3)	0.3197 (3)	0.0182 (6)
H7A	0.8752	0.3364	0.3670	0.022*
H7B	0.7858	0.2527	0.2708	0.022*
C8	1.0080 (3)	0.2501 (3)	0.2374 (3)	0.0165 (6)
H8A	1.0104	0.3275	0.1860	0.020*
H8B	1.0960	0.2494	0.2879	0.020*
C9	1.0049 (3)	0.1299 (3)	0.1576 (3)	0.0188 (6)
H9A	0.9156	0.1291	0.1089	0.023*
H9B	1.0056	0.0524	0.2089	0.023*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
I1	0.02027 (12)	0.02375 (13)	0.02352 (13)	−0.00457 (9)	0.00680 (8)	−0.00334 (8)
Br1	0.02236 (16)	0.02035 (17)	0.01971 (17)	−0.00170 (13)	0.00538 (12)	−0.00201 (12)
O1	0.0161 (10)	0.0142 (11)	0.0224 (11)	0.0028 (9)	0.0045 (9)	0.0058 (9)
C1	0.0183 (15)	0.0124 (14)	0.0232 (15)	0.0015 (13)	0.0018 (12)	0.0035 (13)
C2	0.0141 (14)	0.0138 (15)	0.0267 (16)	0.0030 (12)	0.0016 (12)	−0.0033 (13)
C3	0.0126 (14)	0.0194 (16)	0.0187 (16)	−0.0030 (12)	0.0012 (12)	−0.0031 (12)
C4	0.0201 (15)	0.0132 (15)	0.0209 (16)	−0.0016 (13)	0.0016 (12)	0.0009 (12)
C5	0.0173 (14)	0.0141 (15)	0.0218 (16)	0.0039 (13)	−0.0001 (12)	−0.0017 (12)
C6	0.0132 (13)	0.0134 (14)	0.0157 (14)	−0.0019 (12)	0.0002 (11)	−0.0029 (12)
C7	0.0216 (15)	0.0117 (15)	0.0214 (15)	0.0041 (13)	0.0024 (12)	0.0018 (12)
C8	0.0208 (15)	0.0116 (15)	0.0171 (15)	−0.0005 (12)	0.0023 (12)	0.0015 (11)
C9	0.0175 (14)	0.0183 (16)	0.0206 (16)	−0.0040 (13)	0.0041 (12)	−0.0019 (13)

Geometric parameters (Å, º)

I1—C3	2.101 (3)	C4—H4	0.9300
Br1—C9	1.946 (3)	C5—C6	1.397 (4)
O1—C6	1.376 (3)	C5—H5	0.9300
O1—C7	1.441 (3)	C7—C8	1.524 (4)
C1—C6	1.382 (4)	C7—H7A	0.9700
C1—C2	1.388 (4)	C7—H7B	0.9700
C1—H1	0.9300	C8—C9	1.506 (4)
C2—C3	1.372 (4)	C8—H8A	0.9700
C2—H2	0.9300	C8—H8B	0.9700
C3—C4	1.387 (4)	C9—H9A	0.9700
C4—C5	1.386 (4)	C9—H9B	0.9700
C6—O1—C7	116.9 (2)	O1—C7—C8	106.7 (2)
C6—C1—C2	119.5 (3)	O1—C7—H7A	110.4
C6—C1—H1	120.3	C8—C7—H7A	110.4
C2—C1—H1	120.3	O1—C7—H7B	110.4
C3—C2—C1	120.4 (3)	C8—C7—H7B	110.4
C3—C2—H2	119.8	H7A—C7—H7B	108.6
C1—C2—H2	119.8	C9—C8—C7	111.2 (2)
C2—C3—C4	120.6 (3)	C9—C8—H8A	109.4
C2—C3—I1	119.6 (2)	C7—C8—H8A	109.4
C4—C3—I1	119.8 (2)	C9—C8—H8B	109.4
C5—C4—C3	119.6 (3)	C7—C8—H8B	109.4
C5—C4—H4	120.2	H8A—C8—H8B	108.0
C3—C4—H4	120.2	C8—C9—Br1	110.9 (2)
C4—C5—C6	119.6 (3)	C8—C9—H9A	109.5
C4—C5—H5	120.2	Br1—C9—H9A	109.5
C6—C5—H5	120.2	C8—C9—H9B	109.5
O1—C6—C1	124.6 (3)	Br1—C9—H9B	109.5
O1—C6—C5	115.1 (2)	H9A—C9—H9B	108.0
C1—C6—C5	120.3 (3)
C6—C1—C2—C3	0.1 (4)	C2—C1—C6—O1	−178.5 (3)
C1—C2—C3—C4	−1.1 (4)	C2—C1—C6—C5	0.8 (4)
C1—C2—C3—I1	177.6 (2)	C4—C5—C6—O1	178.6 (3)
C2—C3—C4—C5	1.1 (4)	C4—C5—C6—C1	−0.8 (4)
I1—C3—C4—C5	−177.6 (2)	C6—O1—C7—C8	−178.0 (2)
C3—C4—C5—C6	−0.2 (4)	O1—C7—C8—C9	63.5 (3)
C7—O1—C6—C1	−5.4 (4)	C7—C8—C9—Br1	178.25 (18)
C7—O1—C6—C5	175.3 (2)